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Acetophenone

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Identification
Molecular formula
C8H8O
CAS number
98-86-2
IUPAC name
1-(m-tolyl)ethanone;1-(o-tolyl)ethanone;1-(p-tolyl)ethanone
State
State
Acetophenone is in a liquid state at room temperature. It becomes solid at temperatures below its melting point.
Melting point (Celsius)
20.00
Melting point (Kelvin)
293.15
Boiling point (Celsius)
202.00
Boiling point (Kelvin)
475.15
General information
Molecular weight
120.15g/mol
Molar mass
120.1530g/mol
Density
1.0150g/cm3
Appearence

Acetophenone is a viscous, oily liquid that is colorless and possesses a sweet, pungent odor, similar to that of orange blossoms. It is typically present as a transparent liquid at room temperature and can appear as crystalline when solidified at lower temperatures.

Comment on solubility

Solubility of 1-(m-tolyl)ethanone, 1-(o-tolyl)ethanone, and 1-(p-tolyl)ethanone

The solubility of the tolanyl ethanones can be intriguing due to the subtle differences in their molecular structure influenced by the position of the methyl group on the aromatic ring. Below are some insights into their solubility characteristics:

  • 1-(m-tolyl)ethanone: Exhibits moderate solubility in organic solvents like ethanol and ether, but limited solubility in water due to its hydrophobic aromatic character.
  • 1-(o-tolyl)ethanone: Tends to have higher solubility in organic solvents compared to its meta counterpart, which may be attributed to the steric effects arising from its molecular configuration.
  • 1-(p-tolyl)ethanone: Generally shows similar solubility profiles to 1-(m-tolyl)ethanone, with a slight increase in solubility in polar solvents, indicating that position matters.

Overall, the solubility of these compounds can be summarized as follows:

  1. Soluble in common organic solvents
  2. Poorly soluble in water
  3. Solubility may vary based on the methyl group's position

As a rule of thumb, the greater the molecular interaction with solvents, the higher the solubility. Thus, understanding these nuances can lead to more effective applications in various chemical processes.

Interesting facts

Interesting Facts about 1-(m-tolyl)ethanone, 1-(o-tolyl)ethanone, and 1-(p-tolyl)ethanone

These three compounds, commonly known as substituted ketones, showcase an intriguing aspect of organic chemistry—**isomerism**. Each compound features a different arrangement of the methyltoluene group (tolyl) which affects their chemical properties and reactivity.

Here’s a closer look at some noteworthy points:

  • Isomer Types:
    • 1-(m-tolyl)ethanone: This compound features the m-tolyl (meta-substituted toluene) group, leading to unique steric and electronic properties.
    • 1-(o-tolyl)ethanone: With an o-tolyl (ortho-substituted toluene) structure, this compound exhibits distinct characteristics stemming from the proximity of the substitution on the benzene ring.
    • 1-(p-tolyl)ethanone: The p-tolyl (para-substituted toluene) form often shows different reactivity patterns compared to its ortho and meta counterparts, making it particularly interesting in synthesis.
  • Synthetic Applications:
    • These ketones are often used as intermediates in organic synthesis, providing essential building blocks for pharmaceuticals and various organic compounds.
    • 1-(p-tolyl)ethanone, for example, is valuable in the production of dyes and fragrances, owing to its aromatic structure.
  • Biological Relevance: Some substituted ketones, like those in question, can exhibit interesting biological activities, making them potential candidates for drug development.

In conclusion, 1-(m-tolyl)ethanone, 1-(o-tolyl)ethanone, and 1-(p-tolyl)ethanone highlight a fascinating component of chemical science: the impact of structure on properties and reactivity. As one digs deeper into organic synthesis, understanding these isomers allows for more targeted and efficient applications in various fields, ranging from medicinal chemistry to industrial manufacturing. As the renowned chemist Linus Pauling once said, "The best way to have a good idea is to have lots of ideas," and exploring compounds like these is key to generating new chemical insights.